4-(3-Aminobenzoyl)-1 methylpyrazoles and their use as herbicides

ABSTRACT

What is described are 4-(3-aminobenzoyl)pyrazoles of the general formula (I) and their use as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), R 1  and R 2  are radicals such as hydrogen and organic radicals, such as alkyl, alkenyl and alkynyl. Y is hydrogen or a protective group, such as tosyl.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims priority from EP 07 007 490.1 filed Apr. 12,2007, the content of which is incorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to the technical field of the herbicides, inparticular that of the herbicides for the selective control ofbroad-leaved weeds and weed grasses in crops of useful plants.

2. Description of Related Art

From various publications, it is already known that certainbenzoylpyrazoles have herbicidal properties. Thus, WO 98/42678 and JP11292849 each describe 1-alkyl-4-(3-aminobenzoyl)pyrazoles which can besubstituted in the 2- and 4-position of the phenyl ring by a pluralityof different radicals.

However, the herbicidal activity of the compounds known from thesepublications is frequently insufficient. It is therefore an object ofthe present invention to provide herbicidally active compounds havingherbicidal properties which are better than those of the compoundsdisclosed in the prior art.

SUMMARY OF THE INVENTION

It has now been found that certain 4-benzoylpyrazoles whose phenyl ringcarries a methyl group in the 2-position, a substituted amino group inthe 3-position and a methylsulfonyl group in the 4-position areparticularly suitable for use as herbicides. Part of the subject matterof the present invention are therefore4-(3-aminobenzoyl)-1-methylpyrazoles of the formula (I) or salts thereof

in which

R¹ is hydrogen, (C₁-C₆)-alkyl or (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl,

R² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, di-(C₁-C₄)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl;

Y is hydrogen, (C₁-C₆)-alkylsulfonyl,(C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,thiophenyl-2-sulfonyl, benzoyl, (C₁-C₄)-alkylbenzoyl-(C₁-C₆)-alkyl orbenzyl, each of which is substituted by m identical or differentradicals from the group consisting of halogen, (C₁-C₄)-alkyl and(C₁-C₄)-alkoxy,

m is 0, 1, 2 or 3.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Where Y is hydrogen, the compounds of the formula (I) according to theinvention, depending on external conditions, such as solvent and pH, mayoccur in different tautomeric structures:

Depending on the nature of the substituents, the compounds of thegeneral formula (I) contain an acidic proton which may be removed byreaction with a base. Suitable bases are, for example, hydrides,hydroxides and carbonates of lithium, sodium, potassium, magnesium andcalcium, and also ammonia and organic amines, such as triethylamine andpyridine. It is also possible to form salts by forming adducts withorganic acids, such as formic acid or acetic acid, and inorganic acids,such as phosphoric acid, hydrochloric acid or sulfuric acid. Such saltsalso form part of the subject matter of the invention.

In formula (I) and all subsequent formulae, alkyl radicals with morethan two carbon atoms can be straight-chain or branched. Alkyl radicalsare, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl,pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Halogenis fluorine, chlorine, bromine or iodine. Tosyl is4-methylphenylsulfonyl.

If a group is polysubstituted by radicals, this is to be understood asmeaning that this group is substituted by one or more identical ordifferent of the radicals mentioned.

Depending on the type and the linkage of the substituents, the compoundsof the general formula (I) can exist as stereoisomers. If, for example,one or more asymmetric carbon atoms are present, enantiomers anddiastereomers may occur. Stereoisomers can be contained from themixtures resulting from the preparation by means of customary separationmethods, for example by chromatic separation methods. Likewise,stereoisomers may be prepared selectively by using stereoselectivereactions employing optically active starting materials and/orauxiliaries. The invention also relates to all stereoisomers and theirmixtures which are encompassed by the general formula (I), but notdefined specifically.

Preference is given to compounds of the general formula (I) in which

R¹ is hydrogen or (C₁-C₄)-alkyl,

R² is (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,di-(C₁-C₂)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl;

Y is hydrogen, (C₁-C₃)-alkylsulfonyl,(C₁-C₂)-alkoxy-(C₁-C₄)-alkylsulfonyl, or is phenylsulfonyl,thiophenyl-2-sulfonyl, benzoyl, (C₁-C₄)-alkylbenzoyl-(C₁-C₆)-alkyl orbenzyl, each of which is substituted by m methyl groups,

m is 0 or 1.

Particular preference is given to compounds of the general formula (I)in which

R¹ is hydrogen or (C₁-C₄)-alkyl,

R² is (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,di-(C₁-C₂)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl;

Y is hydrogen.

In all the formulae given below, the substituents and symbols have thesame meaning as described under formula (I), unless defined otherwise.

Compounds according to the invention in which Y is hydrogen can beprepared, for example, by the process shown in scheme 1 and known fromB. S. Jensen, Acta Chem. Scand., 1959, 13, 1668 by base-catalyzedreaction of a benzoyl halide (III) with a pyrazolone (II) or accordingto the process shown in scheme 2 and known, for example, from EP-A 0 186117 by base-catalyzed reaction of a benzoyl halide (III) with apyrazolone (II) and subsequent rearrangement.

According to scheme 3, compounds according to the invention in which Yhas a meaning different from hydrogen are expediently prepared from thecompounds obtainable according to scheme 1 or 2, by base-catalyzedreaction with a suitable acylating agent Y—X of the formula (V) in whichX is a leaving group, such as halogen. Such methods are known inprinciple to the person skilled in the art and described, for example,in DE-A 25 13 750.

Compounds according to the invention can also be prepared according tothe process shown in scheme 4 and known from WO 98/42678 by reacting apyrazolone (II) with a halobenzoic acid (IIIa) and subsequent reactionwith an amine H—NR¹R². Such reactions are known to the person skilled inthe art.

The starting materials used in the above schemes are either commerciallyavailable or can be prepared by methods known per se. Thus, thepyrazolones of the formula (II) can be prepared, for example, by themethods described in EP-A 0 240 001 and J. Prakt. Chem. 315, 382,(1973), and the benzoyl chlorides of the formula (III) can be preparedby the methods described in EP-A 0 527 036, WO 98/42678 and in JP11292849.

The compounds of the formula (I) according to the invention have anexcellent herbicidal activity against a broad range of economicallyimportant monocotyledonous and dicotyledonous harmful plants. The activesubstances control perennial weeds equally well which produce shootsfrom rhizomes, root stocks or other perennial organs and which cannot beeasily controlled. In this context, it generally does not matter whetherthe substances are applied before sowing, pre-emergence orpost-emergence. Some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compoundsaccording to the invention may be mentioned individually as examples,but this is not to be taken to mean a restriction to certain species.The monocotyledonous weed species which are controlled well are, forexample, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria,Setaria and Cyperus species from the annual group, and Agropyron,Cynodon, Imperata and Sorghum or else perennial Cyperus species amongstthe perennial species. In the case of dicotyledonous weed species, thespectrum of action extends to species such as, for example, Galium,Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida,Matricaria and Abutilon from the annual group, and Convolvulus, Cirsium,Rumex and Artemisia among the perennial weeds. Harmful plants which arefound under the specific culture conditions of rice, such as, forexample, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus andCyperus are also controlled outstandingly well by the active substancesaccording to the invention. If the compounds according to the inventionare applied to the soil surface prior to germination, then eitheremergence of the weed seedlings is prevented completely, or the weedsgrow until they have reached the cotyledon stage but growth then comesto a standstill and, after a period of three to four weeks, the plantseventually die completely. When the active substances are appliedpost-emergence to the green parts of the plants, growth also stopsdrastically very soon after the treatment, and the weeds remain at thegrowth stage of the time of application, or, after a certain period oftime, they die completely so that competition by the weeds, which isdetrimental for the crop plants, is thus eliminated at a very earlystage and in a sustained manner. In particular, the compounds accordingto the invention have an outstanding action against Apera spica venti,Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellariamedia, Veronica hederifolia, Veronica persica and Viola tricolor.

Although the compounds according to the invention have an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops such as, for example, wheat,barley, rye, rice, corn, sugar beet, cotton and soybeans, only suffernegligible damage, if any. In particular, they are outstandingly welltolerated in cereals, such as wheat, barley and corn, in particularwheat. This is why the present compounds are highly suitable for theselective control of undesired vegetation in stands of agriculturaluseful plants or of ornamentals.

Owing to their herbicidal properties, the active substances can also beemployed for controlling harmful plants in crops of known plants orgenetically modified plants which are yet to be developed. As a rule,the transgenic plants are distinguished by particularly advantageousproperties, for example by resistances to certain pesticides, especiallycertain herbicides, by resistances to plant diseases or causativeorganisms of plant diseases, such as certain insects or microorganismssuch as fungi, bacteria or viruses. Other particular properties concernfor example the harvested material with regard to quantity, quality,shelf life, composition and specific constituents. Thus, transgenicplants are known which have an increased starch content or whose starchquality has been modified, or whose fatty acid composition in theharvested material is different.

The compounds of the formula (I) according to the invention or theirsalts are preferably employed in economically important transgenic cropsof useful plants and ornamentals, for example cereals such as wheat,barley, rye, oats, millet, rice, cassava and corn, or else crops ofsugar beet, cotton, soybeans, oilseed rape, potato, tomato, pea andother vegetables. The compounds of the formula (I) can preferably beemployed as herbicides in crops of useful plants which are resistant, orhave been genetically modified to be resistant, to the phytotoxiceffects of the herbicides.

Conventional routes for the generation of novel plants which havemodified properties compared with existing plants are, for example,traditional breeding methods and the generation of mutants.Alternatively, novel plants with modified properties can be generatedwith the aid of recombinant methods (see, for example, EP-A-0221044,EP-A-0131624). For example, several cases of the following have beendescribed:

-   -   recombinant modifications of crop plants for the purposes of        modifying the starch synthesized in the plants (for example WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which exhibit resistances to certain        herbicides of the glufosinate type (cf. eg. EP-A-0242236,        EP-A-242246), glyphosate type (WO 92/00377) or of the        sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659)    -   transgenic crop plants, for example cotton, with the ability to        produce Bacillus thuringiensis toxins (Bt toxins), which make        the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972).

A large number of techniques in molecular biology, with the aid of whichnovel transgenic plants with modified properties can be generated, areknown in principle; see, for example, Sambrook et al., 1989, MolecularCloning, A Laboratory Manual, 2^(nd) Ed., Cold Spring Harbor LaboratoryPress, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genesand Clones], VCH Weinheim 2^(nd) Edition 1996 or Christou, “Trends inPlant Science” 1 (1996) 423-431.

To carry out such recombinant manipulations, nucleic acid molecules canbe introduced into plasmids which permit a mutagenesis or a sequencealteration by recombination of DNA sequences. With the aid of theabovementioned standard methods, it is possible, for example, to carryout base substitutions, to remove part sequences or to add natural orsynthetic sequences. The fragments can be provided with adapters orlinkers to link the DNA fragments to each other.

Plant cells with a reduced activity of a gene product can be obtained,for example, by expressing at least one corresponding antisense RNA, asense RNA for achieving a cosuppression effect, or by expressing atleast one suitably constructed ribozyme which specifically cleavestranscripts of the abovementioned gene product.

To this end, it is possible, on the one hand, to use DNA molecules whichencompass all of the coding sequence of a gene product including anyflanking sequences which may be present, but also DNA molecules whichonly encompass portions of the coding sequence, it being necessary forthese portions to be so long as to cause an antisense effect in thecells. Another possibility is the use of DNA sequences which have a highdegree of homology with the coding sequences of a gene product, but arenot completely identical.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, thecoding region can, for example, be linked to DNA sequences which ensurelocalization in a particular compartment. Such sequences are known tothe skilled worker (see, for example, Braun et al., EMBO J. 11 (1992),3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850;Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated by known techniques togive intact plants. In principle, the transgenic plants can be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants. Thus, transgenic plants can be obtained which exhibit modifiedproperties owing to the overexpression, suppression or inhibition ofhomologous (=natural) genes or gene sequences or expression ofheterologous (=foreign) genes or gene sequences.

When using the active substances according to the invention intransgenic crops, effects are frequently observed in addition to theeffects against harmful plants to be observed in other crops, which arespecific for the application in the transgenic crop in question, forexample a modified or specifically widened weed spectrum which can becontrolled, modified application rates which may be employed for theapplication, preferably good combining ability with the herbicides towhich the transgenic crop is resistant, and an effect on the growth andyield of the transgenic crop plants. The invention therefore alsorelates to the use of the compounds according to the invention asherbicides for controlling harmful plants in transgenic crop plants.

The substances according to the invention additionally have outstandinggrowth-regulatory properties in crop plants. They engage in the plants'metabolism in a regulatory fashion and can thus be employed for thetargeted control of plant constituents and for facilitating harvesting,such as, for example, triggering desiccation and stunted growth.Moreover, they are also suitable for generally controlling andinhibiting undesired vegetative growth without destroying the plants inthe process. Inhibiting the vegetative growth plays an important role inmany monocotyledonous and dicotyledonous crops since lodging can bereduced, or prevented completely, hereby.

The compounds according to the invention can be employed in the form ofwettable powders, emulsifiable concentrates, sprayable solutions, dustsor granules in the customary preparations. The invention thereforefurthermore relates to herbicidal compositions comprising compounds ofthe formula (I). The compounds of the formula (I) can be formulated invarious ways, depending on the prevailing biological and/orchemico-physical parameters. Examples of suitable formulations which arepossible are: wettable powders (WP), water-soluble powders (SP),water-soluble concentrates, emulsifiable concentrates (EC), emulsions(EW), such as oil-in-water and water-in-oil emulsions, sprayablesolutions, suspension concentrates (SC), oil- or water-baseddispersions, oil-miscible solutions, capsule suspensions (CS), dusts(DP), seed-dressing products, granules for spreading and soilapplication, granules (GR) in the form of microgranules, spray granules,coated granules and adsorption granules, water-dispersible granules(WG), water-soluble granules (SG), ULV formulations, microcapsules andwaxes. These individual formulation types are known in principle and aredescribed, for example, in Winnacker-Küchler, “Chemische Technologie”[Chemical Engineering], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986,Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd.London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Pubi. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hauser Verlag Munich, 4th Ed.1986.

Wettable powders are preparations which are uniformly dispersible inwater and which, in addition to the active substance, also contain ionicand/or nonionic surfactants (wetters, dispersants), for examplepolyoxyethylated alkylphenols, polyoxyethylated fatty alcohols,polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates,alkanesulfonates, alkylbenzenesulfonates, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodium lignosulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate, inaddition to a diluent or inert substance. To prepare the wettablepowders, the herbicidal active substances are ground finely, for examplein customary equipment such as hammer mills, blowing mills and air-jetmills, and simultaneously or subsequently mixed with the formulationauxiliaries.

Emulsifiable concentrates are prepared by dissolving the activesubstance in an organic solvent, e.g. butanol, cyclohexanone,dimethylformamide, xylene or else higher-boiling aromatics orhydrocarbons or mixtures of the organic solvents with addition of one ormore ionic and/or nonionic surfactants (emulsifiers). Examples ofemulsifiers which can be used are: calcium alkylarylsulfonate salts suchas calcium dodecylbenzenesulfonate, or nonionic emulsifiers such asfatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide/ethylene oxide condensates, alkylpolyethers, sorbitan esters such as, for example, sorbitan fatty acidesters or polyoxyethylene sorbitan esters such as, for example,polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active substance with finely dividedsolid materials, for example talc, natural clays such as kaolin,bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water-based or oil-based. They can beprepared for example by wet-grinding by means of customary bead mills,if appropriate with addition of surfactants, as have already beenmentioned for example above in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if appropriate, surfactants as havealready been mentioned for example above in the case of the otherformulation types.

Granules can be prepared either by spraying the active substance ontoadsorptive, granulated inert material or by applying active substanceconcentrates to the surface of carriers such as sand, kaolinites orgranulated inert material with the aid of adhesives, for examplepolyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitableactive substances can also be granulated in the fashion which isconventional for the production of fertilizer granules, if desired as amixture with fertilizers.

Water-dispersible granules are generally prepared by customary methodssuch as spray drying, fluidized-bed granulation, disk granulation,mixing with high-speed stirrers and extrusion without solid inertmaterial.

To prepare disk granules, fluidized-bed granules, extruder granules andspray granules, see, for example methods in “Spray-Drying Handbook” 3rded. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”,Chemical and Engineering 1967, pages 147 et seq.; “Perry's ChemicalEngineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details on the formulation of crop protection agents see,for example G. C. Klingman, “Weed Control as a Science”, John Wiley andSons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans,“Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications,Oxford, 1968, pages 101-103.

As a rule, the agrochemical preparations comprise 0.1 to 99% by weight,in particular 0.1 to 95% by weight, of active substance of the formula(I). In wettable powders, the active substance concentration is, forexample, approximately 10 to 90% by weight, the remainder to 100% byweight being composed of customary formulation constituents. In the caseof emulsifiable concentrates, the active substance concentration canamount to approximately 1 to 90, preferably 5 to 80% by weight.Formulations in the form of dusts comprise 1 to 30% by weight of activesubstance, preferably in most cases 5 to 20% by weight of activesubstance, and sprayable solutions comprise approximately 0.05 to 80,preferably 2 to 50% by weight of active substance. In the case ofwater-dispersible granules, the active substance content depends partlyon whether the active compound is in liquid or solid form and on thegranulation auxiliaries, fillers and the like which are being used. Inthe case of the water-dispersible granules, for example, the activesubstance content is between 1 and 95% by weight, preferably between 10and 80% by weight.

In addition, the active substance formulations mentioned comprise, ifappropriate, the tackifiers, wetters, dispersants, emulsifiers,penetrants, preservatives, antifreeze agents, solvents, fillers,carriers, colorants, antifoams, evaporation inhibitors, and pH andviscosity regulators which are conventional in each case.

Based on these formulations, it is also possible to prepare combinationswith other pesticidally active substances such as, for example,insecticides, acaricides, herbicides, fungicides, and with safeners,fertilizers and/or growth regulators, for example in the form of areadymix or a tank mix.

Active substances which can be employed in combination with the activesubstances according to the invention in mixed formulations or in thetank mix are, for example, known active substances as are described, forexample, in Weed Research 26, 441-445 (1986) or “The Pesticide Manual”,11th edition, The British Crop Protection Council and the Royal Soc. ofChemistry, 1997 and literature cited therein. Known herbicides whichmust be mentioned, and can be combined with the compounds of the formula(I), are, for example, the following active substances (note: thecompounds are either designated by the common name according to theInternational Organization for Standardization (ISO) or using thechemical name, if appropriate together with a customary code number):acetochlor; acifluorfen; aclonifen; AKH 7088, i.e.[[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]aceticacid and its methyl ester; alachlor; alloxydim; ametryn; amidosulfuron;amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazine;azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516H, i.e.5-fluorine-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin;benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap;benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox;bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos;busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin;butylate; cafenstrole (CH-900); carbetamide; cafentrazone; CDAA, i.e.2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyldiethyidithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl,chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl;chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron;chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl;chlorthiamid; cinmethylin; cinosulfuron; clethodim; clodinafop and itsester derivatives (for example clodinafop-propargyl); clomazone;clomeprop; cloproxydim; clopyralid; cumyluron (JC 940); cyanazine;cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop andits ester derivatives (for example butylester, DEH-112); cyperquat;cyprazine; cyprazole; daimuron; 2,4-DB; dalapon; desmedipham; desmetryn;di-allate; dicamba; dichlobenil; dichlorprop; diclofop and its esterssuch as diclofop-methyl; diethatyl; difenoxuron; difenzoquat;diflufenican; dimefuron; dimethachlor; dimethametryn; dimethenamid(SAN-582H); dimethazone, clomazon; dimethipin; dimetrasulfuron,dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat;dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e.5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide;endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl;ethidimuron; ethiozin; ethofumesate; F5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide;ethoxyfen and its esters (for example ethylester, HN-252); etobenzanid(HW 52); fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and theiresters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim;fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P andtheir esters, for example fluazifop-butyl and fluazifop-P-butyl;fluchloralin; flucarbazoue; flufenacet; flumetsulam; flumeturon;flumiclorac and its esters (for example pentylester, S-23031);flumioxazin (S-482); flumipropyn; flupoxam (KNW-739); fluorodifen;fluoroglycofen-ethyl; flupropacil (UBIC-4243); fluridone;flurochloridone; fluroxypyr; flurtamone; fomesafen; foramsulfuron;fosamine; furyloxyfen; glufosinate; glyphosate; halosafen; halosulfuronand its esters (for example methylester, NC-319); haloxyfop and itsesters; haloxyfop-P (═R-haloxyfop) and its esters; hexazinone; imazapyr;imazamethabenz-methyl; imazaquin and salts such as the ammonium salt;ioxynil; imazethamethapyr; imazethapyr; imazosulfuron;iodosulfuron-methyl-sodium; isocarbamid; isopropalin; isoproturon;isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil;linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; mesosulfuron;mesotrione; metamitron; metazachlor; metham; methabenzthiazuron;methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron;metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin;metsulfuron-methyl; MH; molinate; monalide; monolinuron; monuron;monocarbamide dihydrogensulfate; MT 128, i.e.6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide;naproanilide; napropamide; naptalam; NC 310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon;nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen;norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon;oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone;phenisopham; phenmedipham; picloram; pinoxaden; piperophos;piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl;procyazine; prodiamine; profluralin; proglinazine-ethyl; prometon;prometryn; propachlor; propanil; propaquizafop and its esters;propazine; propham; propisochlor; propoxycarbazone; propyzamide;prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor;pyrazolinate; pyrazon; pyrasulfotole; pyrazosulfuron-ethyl; pyrazoxyfen;pyridate; pyrithiobac (KIH-2031); pyroxofop and its esters (for examplepropargyl ester); quinclorac; quinmerac; quinofop and its esterderivatives, quizalofop and quizalofop-P and their ester derivatives forexample quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron;rimsulfuron (DPX-E 9636); S 275, i.e.2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e.2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoicacid and its methyl ester; sulcotrione; sulfentrazon (FMC-97285,F-6285); sulfazuron; sulfometuron-methyl; sulfosate (ICI-A0224); TCA;tebutam (GCP-5544); tebuthiuron; tembotrione; terbacil; terbucarb;terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e.N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide;thenylchlor (NSK-850); thiazafluron; thiencarbazone; thiazopyr(Mon-13200); thidiazimin (SN-24085); thiobencarb; thifensulfuron-methyl;tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide;tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin;triflusulfuron and esters (for example methyl ester, DPX-66037);trimeturon; tsitodef; vernolate; WL 110547, i.e.5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; UBH-509; D-489; LS82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535;DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 andKIH-2023.

For use, the formulations, which are present in commercially availableform, are if appropriate diluted in the customary manner, for exampleusing water in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules. Preparations in the form ofdusts, soil granules, granules for spreading and sprayable solutions areusually not diluted any further with other inert substances prior touse.

The application rate required of the compounds of the formula (I) varieswith the external conditions such as, inter alia, temperature, humidityand the nature of the herbicide used. It can vary within wide limits,for example between 0.001 and 1.0 kg/ha or more of active substance, butit is preferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES Preparation of4-[3-cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoyl]-5-hydroxy-1-methylpyrazoleStep 1: 3-cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoic acid

5.0 g (22 mmol) of 3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid weredissolved in 25.0 ml (356 mmol) of cyclopropylamine. With stirring, themixture was then heated in an autoclave at 120° C. for 1 day, and thencooled to room temperature (RT), acidified with a mixture of ice-waterand conc. sulfuric acid and extracted with ethyl acetate. The combinedorganic phases were dried over MgSO₄, and the solvent was removed underreduced pressure. The residue was purified by preparative HPLC. Thisgave 1.8 g of a beige solid of purity of 95%.

¹H-NMR: δ [CDCl₃] 0.57-0.63 (m, 2H), 0.76-0.82 (m, 2H), 2.68 (s, 3H),2.80-2.85 (m, 1H), 3.01 (s, 3H), 7.45 (d, 1H), 7.75 (d, 1H)

Step 2:4-[3-cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoyl]-5-hydroxy-1-methylpyrazole

Under nitrogen, 0.50 g (1.9 mmol) of3-cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoic acid, 0.24 g (2.4mmol) of 5-hydroxy-1-methylpyrazole and 0.43 g (2.2 mmol) of1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride weredissolved in dry CH₃CN. The mixture was stirred at RT for 5 h. 0.52 ml(3.7 mmol) of NEt₃, 0.10 ml (0.7 mmol) of Me₃SiCN and a spatula tip ofKCN were added, and the mixture was stirred at RT for 1 day. The solventwas removed under reduced pressure, and the residue was taken up inCH₂Cl₂ and 10% strength H₂SO₄. The aqueous phase was extracted withCH₂Cl₂. The organic phases were dried over MgSO₄, and the solvent wasremoved under reduced pressure. The residue was purified by preparativeHPLC. This gave 0.19 g of a beige solid of a purity of 90%.

¹H-NMR: δ [CDCl₃] 0.60-0.65 (m, 2H), 0.72-0.83 (m, 2H), 2.48 (s, 3H),2.80-2.88 (m, 1H), 3.01 (s, 3H), 3.72 (s, 3H), 6.97 (d, 1H), 7.37 (s,1H), 7.76 (d, 1H).

Preparation of4-[3-allylamino-2-methyl-4-(methylsulfonyl)benzoyl]-5-hydroxy-1-methylpyrazoleStep 1: 3-allylamino-2-methyl-4-(methylsulfonyl)benzoic acid

4.0 g (17 mmol) of 3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid weredissolved in 12.9 ml (172 mmol) of allylamine. The mixture was heated atreflux for 5 days and allowed to stand for 2 days. 10 ml (134 mmol) ofallylamine and 15 ml of water were added, and the mixture was heated atreflux for 14 days, cooled to RT, added to ice, acidified with 10%strength sulfuric acid and extracted twice with ethyl acetate. Thecombined organic phases were dried over MgSO₄, and the solvent wasremoved under reduced pressure. The residue was crystallized fromdiethyl ether. This gave 4.2 g of a yellow solid of a purity of 88%.

¹H-NMR: δ [CDCl₃] 2.48 (s, 3H), 3.08 (s, 3H), 3.76-3.81 (m, 2H),5.17-5.24 (m, 1H), 5.31-5.39 (m, 1H), 5.92-6.07 (m, 1H), 7.47 (d, 1H),7.76 (d, 1H)

Step 2:4-[3-allylamino-2-methyl-4-(methylsulfonyl)benzoyl]-5-hydroxy-1-methylpyrazole

Under nitrogen, 0.31 g (1.2 mmol) of3-allylamino-2-methyl-4-(methylsulfonyl)benzoic acid, 0.15 g (1.5 mmol)of 5-hydroxy-1-methylpyrazole and 0.27 g (1.4 mmol) of1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride weredissolved in dry CH₃CN. The mixture was stirred at RT for 5 h. 0.32 ml(2.3 mmol) of NEt₃, 0.06 ml (0.5 mmol) of Me₃SiCN and a spatula tip ofKCN were added, and the mixture was stirred at RT for 1 day. The solventwas removed under reduced pressure, and the residue was taken up inCH₂Cl₂ and 10% strength H₂SO₄. The aqueous phase was removed andextracted once with CH₂Cl₂. The combined organic phases were dried overMgSO₄, and the solvent was removed under reduced pressure. The residuewas crystallized from tert-butyl methyl ether. This gave 0.15 g of acolorless solid of a purity of 100%.

¹H-NMR: δ [CDCl₃] 2.31 (s, 3H), 3.10 (s, 3H), 3.71 (s, 3H), 3.83-3.88(m, 2H), 5.20-5.25 (m, 1H), 5.33-5.40 (m, 1H), 5.95-6.05 (m, 1H), 7.08(d, 1H), 7.35 (s, 1H), 7.84 (d, 1H)

The examples given in the tables which follow were prepared analogouslyto the methods mentioned above, or can be obtained analogously to themethods mentioned above. These compounds are particularly preferred.

The abbreviations used denote:

TABLE A Compounds according to the invention of the general formula (I)

Physical data: No. R¹ R² Y ^(1+lH-NMR: δ [CDCl) ₃] 1 H Me H 2.34 (s,3H), 3.01 (s, 3H), 3.09 (s, 3H), 3.71 (s, 3H), 7.05 (d, 1H) 7.36 (s, 1H)7.82 (d, 1H) 2 H Et H 1.30 (t, 3H), 2.32 (s, 3H), 3.11 (s, 3H), 3.27 (q,2H), 3.71 (s, 3H), 7.05 (d, 1H), 7.36 (s, 1H), 7.82 (d, 1H) 3 H n-Pr H1.03 (t, 3H), 1.66-1.76 (m, 2H), 2.32 (s, 3H), 3.11 (s, 3H) 3.16-3.21(m, 2H), 3.71 (s, 3H), 7.04 (d, 1H), 7.37 (s, 1H), 7.82 (d, 1H) 4 H i-PrH 1.22 (d, 6H), 2.28 (s, 3H), 3.12 (s, 3H) 3.68- 3.82 (m, 1H), 3.71 (s,3H), 7.03 (d, 1H), 7.34 (s, 1H), 7.82 (d, 1H) 5 H c-Pr H 0.60-0.65 (m,2H), 0.72-0.83 (m, 2H), 2.48 (s, 3H), 2.80-2.88 (m, 1H), 3.01 (s, 3H),3.72 (s, 3H), 6.97 (d, 1H), 7.37 (s, 1H), 7.76 (d, 1H) 6 H n-Bu H 7 Hs-Bu H 0.99 (t, 3H), 1.17 (d, 3H), 1.45-1.57 (m, 1H), 1.60-1.72 (m, 1H),2.28 (s, 3H), 3.12 (s, 3H), 3.52-3.61 (m, 1H), 3.73 (s, 3H), 7.03 (d,1H), 7.39 (s, 1H), 7.82 (d, 1H) 8 H i-Bu H 1.05 (d, 6H), 1.87-1.97 (m,1H), 2.32 (s, 3H), 3.03 (d, 2H) 3.09 (s, 3H) 3.71 (s, 3H) 7.04 (d, 1H)7.36 (s, 1H), 7.82 (d, 1H) 9 H t-Bu H 10 H n-pentyl H 11 H Allyl H 2.31(s, 3H), 3.10 (s, 3H), 3.71 (s, 3H), 3.83- 3.88 (m, 2H), 5.20-5.25 (m,1H), 5.33-5.40 (m, 1H), 5.95-6.05 (m, 1H), 7.08 (d, 1H), 7.35 (s, 1H),7.84 (d, 1H) 12 H CH═CH₂ H 13 H CH₂C≡CH H 14 H CH₂-c-Pr H 0.26-0.30 (m,2H), 0.57-0.63 (m, 2H), 1.05- 1.16 (m, 1H), 2.30 (s, 3H), 3.09 (d, 2H),3.14 (s, 3H), 3.71 (s, 3H), 7.05 (d, 1H), 7.37 (s, 1H), 7.82 (d, 1H) 15H CH(CH₃)-c-Pr H 16 H CH₂O-Me H 17 H CH₂O-Et H 18 H CH₂O-i-Pr H 19 H(CH₂)₂O-Me H 2.32 (s, 3H), 3.21 (s, 3H), 3.39-3.43 (m, 2H), 3.41 (s,3H), 3.59-3.63 (m, 2H), 3.72 (s, 3H), 7.08 (d, 1H), 7.37 (s, 1H), 7.84(d, 1H) 20 H (CH₂)₂O-Et H 1.24 (t, 3H), 2.32 (s, 3H), 3.20 (s, 3H),3.37- 3.42 (m, 2H), 3.55 (q, 2H), 3.62-3.68 (m, 2H), 3.71 (s, 3H), 7.07(d, 1H), 7.37 (s, 1H), 7.84 (d, 1H) 21 H (CH₂)₂O-i-Pr H 1.21 (d, 6H),2.32 (s, 3H), 3.21 (s, 3H), 3.37- 3.41 (m, 2H), 3.64-3.74 (m, 3H), 3.71(s, 3H), 7.07 (d, 1H), 7.37 (s, 1H), 7.84 (d, 1H) 22 H CH(Me)CH₂O-Me H23 H CH(Me)CH₂O-Et H 24 H CH(Me)CH₂O-i-Pr H 25 H CH₂CH(Me)O-Me H 26 HCH₂CH(Me)O-Et H 27 H CH₂CH(Me)O-i-Pr H 28 H (CH₂)₃O-Me H 1.91-2.00 (m,2H), 2.33 (s, 3H), 3.13 (s, 3H), 3.30 (t, 2H), 3.37 (s, 3H), 3.55 (t,2H), 3.71 (s, 3H), 7.05 (d, 1H), 7.36 (s, 1H), 7.84 (d, 1H) 29 H(CH₂)₃O-Et H 1.21 (t, 3H), 1.90-1.97 (m, 2H), 2.33 (s, 3H), 3.12 (s,3H), 3.32 (t, 2H), 3.51 (q, 2H), 3.59 (t, 2H), 3.71 (s, 3H), 7.08 (d,1H), 7.36 (s, 1H), 7.83 (d, 1H) 30 H (CH₂)₃O-i-Pr H 31 H(CH₂)₂O-(CH₂)₂O-Me H 2.31 (s, 3H), 3.21 (s, 3H), 3.37 (s, 3H), 3.41-3.44 (m, 2H), 3.55-3.59 (m, 2H), 3.65-3.68 (m, 2H), 3.70-3.74 (m, 2H),3.71 (s, 3H), 7.08 (d, 1H), 7.37 (s, 1H), 7.85 (d, 1H) 32 H(CH₂)₂O—(CH₂)₂O-Et H 33 H (CH₂)₃O—(CH₂)₂O-Me H 34 H (CH₂)₃O—(CH₂)₂O-Et H35 H (CH₂)₂O—(CH₂)₃O-Me H 36 H (CH₂)₂O—(CH₂)₃O-Et H 37 H CH₂CH(OMe)₂ H2.32 (s, 3H), 3.20 (s, 3H), 3.37 (d, 2H), 3.43 (s, 6H), 3.71 (s, 3H),4.54 (t, 1H), 7.07 (d, 1H), 7.36 (s, 1H), 7.84 (d, 1H) 38 H CH₂CH(OEt)₂H 1.24 (t, 6H), 2.32 (s, 3H), 3.20 (s, 3H), 3.36 (d, 2H), 3.54-3.66 (m,2H), 3.71 (s, 3H) 3.68- 3.82 (m, 2H), 4.68 (t, 1H), 7.07 (d, 1H), 7.36(s, 1H), 7.83 (d, 1H) 39 H CH₂CH(OMe)(OEt) H 40 H (CH₂)₂CH(OMe)₂ H1.95-2.03 (m, 2H), 2.32 (s, 3H), 3.14 (s, 3H), 3.27 (t, 2H), 3.38 (s,6H), 3.71 (s, 3H), 4.57 (t, 1H), 7.08 (d, 1H), 7.37 (s, 1H), 7.84 (d,1H) 41 H (CH₂)₂CH(OEt)₂ H 1.22 (t, 6H), 1.96-2.03 (m, 2H), 2.33 (s, 3H),3.14 (s, 3H), 3.29 (t, 2H), 3.48-3.58 (m, 2H), 3.64-3.74 (m, 2H), 3.71(s, 3H), 4.68 (t, 1H), 7.08 (d, 1H), 7.36 (s, 1H), 7.84 (d, 1H) 42 H(CH₂)₂CH(OMe)(OEt) H 43 Me Me H 2.38 (s, 3H), 2.92 (s, 6H), 3.29 (s,3H), 3.71 (s, 3H), 7.33 (s, 1H), 7.40 (d, 1H), 8.03 (d, 1H) 44 Me Et H1.21 (t, 3H), 2.36 (s, 3H), 2.88 (s, 3H), 3.11- 3.32 (m, 2H), 3.32 (s,3H), 3.72 (s, 3H), 7.34 (s, 1H), 7.39 (d, 1H), 8.05 (d, 1H) 45 Me n-Pr H0.92 (t, 3H), 1.60-1.76 (m, 2H), 2.37 (s, 3H), 2.89 (s, 3H), 2.95-3.18(m, 2H), 3.32 (s, 3H), 3.74 (s, 3H), 7.36 (d, 1H), 7.38 (s, 1H), 8.05(d, 1H) 46 Me i-Pr H 1.00 (d, 3H), 1.29 (d, 3H), 2.36 (s, 3H), 2.88 (s,3H), 3.33 (s, 3H), 3.52-3.62 (m, 1H), 3.73 (s, 3H), 7.32 (s, 1H), 7.38(d, 1H), 8.08 (d, 1H) 47 Me c-Pr H 48 Me n-Bu H 49 Me s-Bu H 50 Me i-BuH 51 Me t-Bu H 52 Me n-pentyl H 53 Me Allyl H 54 Me CH═CH₂ H 55 MeCH₂C≡CH H 56 Me CH₂-c-Pr H 0.11-0.18 (m, 1H), 0.18-0.26 (m, 1H), 0.43-0.53 (m, 1H), 0.58-0.67 (m, 1H), 1.07-1.18 (m, 1H), 2.34 (s, 3H),2.67-2.76 (m, 1H), 3.00 (s, 3H), 3.28-3.34 (m, 1H), 3.37 (s, 3H), 3.71(s, 3H), 7.33 (s, 1H), 7.39 (d, 1H), 8.05 (d, 1H) 57 Me CH(CH₃)-c-Pr H58 Me CH₂O-Me H 59 Me CH₂O-Et H 60 Me CH₂O-i-Pr H 61 Me (CH₂)₂O-Me H2.37 (s, 3H), 2.95 (s, 3H), 3.22-3.49 (m, 2H), 3.34 (s, 3H), 3.37 (s,3H), 3.63-3.73 (m, 2H), 3.71 (s, 3H), 7.34 (s, 1H), 7.39 (d, 1H), 8.05(d, 1H) 62 Me (CH₂)₂O-Et H 1.27 (t, 3H), 2.38 (s, 3H), 2.95 (s, 3H),3.22- 3.32 (m, 1H), 3.38 (s, 3H), 3.41-3.49 (m, 1H), 3.49 (q, 2H),3.67-3.74 (m, 2H), 3.72 (s, 3H), 7.33 (s, 1H), 7.39 (d, 1H), 8.05 (d,1H) 63 Me (CH₂)₂O-i-Pr H 64 Me CH(Me)CH₂O-Me H 65 Me CH(Me)CH₂O-Et H 66Me CH(Me)CH₂O-i-Pr H 67 Me CH₂CH(Me)O-Me H 68 Me CH₂CH(Me)O-Et H 69 MeCH₂CH(Me)O-i-Pr H 70 Me (CH₂)₃O-Me H 1.89-2.01 (m, 2H), 2.37 (s, 3H),2.91 (s, 3H), 3.07-3.18 (m, 1H), 3.21-3.33 (m, 1H), 3.30 (s, 3H), 3.32(s, 3H), 3.38-3.47 (m, 2H), 3.71 (s, 3H), 7.32 (s, 1H), 7.38 (d, 1H),8.02 (d, 1H) 71 Me (CH₂)₃O-Et H 72 Me (CH₂)₃O-i-Pr H 73 Me(CH₂)₂O-(CH₂)₂O-Me H 74 Me (CH₂)₂O-(CH₂)₂O-Et H 75 Me (CH₂)₃O-(CH₂)₂O-MeH 76 Me (CH₂)₃O-(CH₂)₂O-Et H 77 Me (CH₂)₂O-(CH₂)₃O-Me H 78 Me(CH₂)₂O-(CH₂)₃O-Et H 79 Me CH₂CH(OMe)₂ H 80 Me CH₂CH(OEt)₂ H 81 MeCH₂CH(OMe)(OEt) H 82 Me (CH₂)₂CH(OMe)₂ H 83 Me (CH₂)₂CH(OEt)₂ H 84 Me(CH₂)₂CH(OMe)(OEt) H 85 H Et n-Pr-SO₂ 1.18 (t, 3H), 1.30 (t, 3H),2.03-2.17 (m, 2H), 2.26 (s, 3H), 3.11 (s, 3H), 3.26 (q, 2H), 3.63- 3.70(m, 2H), 3.89 (s, 3H), 5.50 (br, 1H), 6.97 (d, 1H), 7.50 (s, 1H), 7.80(d, 1H) 86 H Et Me-O(CH₂)₂—SO₂ 1.30 (t, 3H), 2.25 (s, 3H), 3.11 (s, 3H),3.26 (q, 2H), 3.45 (s, 3H), 3.89 (s, 3H), 3.97-4.09 (m, 4H), 5.50 (br,1H), 6.96 (d, 1H), 7.47 (s, 1H), 7.82 (d, 1H) 87 H Et Ph-SO2 1.29 (t,3H), 2.21 (s, 3H), 3.09 (s, 3H), 3.37 (q, 2H), 3.82 (s, 3H), 6.82 (d,1H), 7.58-7.64 (m, 3H), 7.66-7.79 (m, 2H), 7.89-7.95 (m, 2H) 88 H Et4-Me-Ph-SO_(s2) 1.29 (t, 3H), 2.21 (s, 3H), 2.46 (s, 3H), 3.08 (s, 3H),3.24 (q, 2H), 3.80 (s, 3H), 5.45 (br, 1H), 6.84 (d, 1H), 7.37 (d, 2H),7.62 (s, 1H), 7.69 (d, 1H), 7.76 (d, 2H) 89 H Et

1.29 (t, 3H), 2.21 (s, 3H), 3.09 (s, 3H), 3.24 (q, 2H), 3.82 (s, 3H),5.45 (br, 1H), 6.86 (d, 1H), 7.18-7.22 (m, 1H), 7.58 (s, 1H), 7.72 (d,1H), 7.79-7.82 (m, 1H), 7.83-7.87 (m, 1H) 90 H Et Ph-C(O) 1.23 (t, 3H),2.21 (s, 3H), 2.89 (s, 3H), 3.13 (q, 2H), 3.75 (s, 3H), 5.28 (br, 1H),6.98 (d, 1H), 7.45-7.53 (m, 2H), 7.61 (d, 1H), 7.66- 7.72 (m, 1H), 7.86(s, 1H), 7.89-7.96 (m, 2H) 91 H Et 4-Me-Ph-C(O)—CH₂ 1.26 (t, 3H), 2.15(s, 3H), 2.42 (s, 3H), 3.08 (s, 3H), 3.22 (q, 2H), 3.89 (s, 3H), 5.45(br, 1H), 6.14 (s, 2H), 6.88 (d, 1H), 7.24 (s, 1H), 7.29 (d, 2H), 7.74(d, 1H), 7.82 (d, 2H) 92 H (CH₂)₂O-Me n-Pr-SO₂ 1.17 (t, 3H), 2.01-2.16(m, 2H), 2.26 (s, 3H), 3.20 (s, 3H), 3.36-3.43 (m, 2H), 3.39 (s, 3H),3.58-3.68 (m, 4H), 3.89 (s, 3H), 5.76 (br, 1H), 6.99 (d, 1H), 7.50 (s,1H), 7.83 (d, 1H) 93 H (CH₂)₂O-Me Me-O(CH₂)₂—SO₂ 2.25 (s, 3H), 3.21 (s,3H), 3.37-3.42 (m, 2H), 3.39 (s, 3H), 3.45 (s, 3H), 3.58-3.63 (m, 2H),3.89 (s, 3H), 3.97-4.06 (m, 4H), 5.76 (br, 1H), 7.00 (d, 1H), 7.49 (s,1H), 7.83 (d, 1H) 94 H (CH₂)₂O-Me Ph-SO₂ 2.22 (s, 3H), 3.18 (s, 3H),3.35-3.42 (m, 2H), 3.40 (s, 3H), 3.57-3.63 (m, 2H), 3.82 (s, 3H), 5.74(br, 1H), 6.84 (d, 1H), 7.57-7.63 (m, 3H), 7.68-7.79 (m, 2H), 7.87-7.92(m, 2H) 95 H (CH₂)₂O-Me 4-Me-Ph-SO₂ 2.22 (s, 3H), 2.46 (s, 3H), 3.18 (s,3H), 3.34- 3.42 (m, 2H), 3.41 (s, 3H), 3.57-3.63 (m, 2H), 3.82 (s, 3H),5.75 (br, 1H), 6.84 (d, 1H), 7.37 (d, 2H), 7.63 (s, 1H), 7.70 (d, 1H),7.72 (d, 2H) 96 H (CH₂)₂O-Me

2.22 (s, 3H), 3.18 (s, 3H), 3.34-3.42 (m, 2H), 3.40 (s, 3H), 3.57-3.63(m, 2H), 3.82 (s, 3H), 5.71 (br, 1H), 6.87 (d, 1H), 7.17-7.22 (m, 1H),7.60 (s, 1H), 7.74 (d, 1H), 7.76-7.80 (m, 1H), 7.83-7.87 (m, 1H) 97 H(CH₂)₂O-Me Ph-C(O) 2.21 (s, 3H), 3.00 (s, 3H), 3.24-3.30 (m, 2H), 3.37(s, 3H), 3.50-3.55 (m, 2H), 3.75 (s, 3H), 5.55 (br, 1H), 6.92 (d, 1H),7.50 (t, 2H), 7.63 (d, 1H), 7.66-7.72 (m, 1H), 7.84 (s, 1H), 7.92- 7.97(m, 2H) 98 H (CH₂)₂O-Me 4-Me-Ph-C(O)—SO₂ 2.16 (s, 3H), 2.42 (s, 3H),3.17 (s, 3H), 3.32- 3.41 (m, 2H), 3.38 (s, 3H), 3.54-3.61 (m, 2H), 3.89(s, 3H), 5.68 (br, 1H), 6.13 (s, 2H), 6.91 (d, 1H), 7.23 (s, 1H), 7.29(d, 2H), 7.77 (d, 1H), 7.82 (d, 2H) 99 Me Me n-Pr-SO₂ 1.18 (t, 3H),2.03-2.16 (m, 2H), 2.34 (s, 3H), 2.92 (s, 6H), 3.29 (s, 3H), 3.60-3.67(m, 2H), 3.89 (s, 3H), 7.33 (d, 1H), 7.49 (s, 1H), 8.01 (d, 1H) 100 MeMe Me-O(CH₂)₂—SO₂ 2.34 (s, 3H), 2.92 (s, 6H), 3.29 (s, 3H), 3.45 (s,3H), 3.91 (s, 3H), 4.01 (s, 4H), 7.33 (d, 1H), 7.47 (s, 1H), 8.01 (d,1H) 101 Me Me Ph-SO₂ 2.33 (s, 3H), 2.92 (s, 6H), 3.29 (s, 3H), 3.76 (s,3H), 7.20 (d, 1H), 7.59-7.68 (m, 2H), 7.63 (s, 1H), 7.72-7.80 (m, 1H),7.84-7.89 (m, 2H), 7.92 (d, 1H) 102 Me Me 4-Me-Ph-SO₂ 2.33 (s, 3H), 2.47(s, 3H), 2.92 (s, 6H), 3.29 (s, 3H), 3.75 (s, 3H), 7.18 (d, 1H), 7.41(d, 2H), 7.63 (s, 1H), 7.71 (d, 2H), 7.92 (d, 1H) 103 Me Me

2.32 (s, 3H), 2.92 (s, 6H), 3.29 (s, 3H), 3.78 (s, 3H), 7.18-7.24 (m,2H), 7.62 (s, 1H), 7.76- 7.80 (m, 1H), 7.84-7.88 (m, 1H), 7.93 (d, 1H)104 Me Me Ph-C(O) 2.26 (s, 3H), 2.72 (s, 6H), 3.05 (s, 3H), 3.74 (s,3H), 7.29 (d, 1H), 7.46-7.54 (m, 2H), 7.64- 7.72 (m, 1H), 7.86 (d, 1H),7.87 (s, 1H), 7.88- 7.92 (m, 2H) 105 Me Me 4-Me-Ph-C(O)—CH₂ 2.21 (s,3H), 2.42 (s, 3H), 2.88 (s, 6H), 3.26 (s, 3H), 3.90 (s, 3H), 6.14 (s,2H), 7.18 (s, 1H), 7.22 (d, 1H), 7.29 (d, 2H), 7.82 (d, 2H), 7.95 (d,1H)

B. FORMULATION EXAMPLES

1. Dust

A dust is obtained by mixing 10 parts by weight of a compound of generalformula (I) and 90 parts by weight of talc as inert substance andcomminuting the mixture in a hammer mill.

2. Dispersible Powder

A wettable powder which is readily dispersible in water is obtained bymixing 25 parts by weight of a compound of general formula (I), 64 partsby weight of kaolin-containing quartz as inert material, 10 parts byweight of potassium lignosulfonate and 1 part by weight of sodiumoleoylmethyltauride as wetter and dispersant, and grinding the mixturein a pinned-disk mill.

3. Dispersion Concentrate

A dispersion concentrate which is readily dispersible in water isobtained by mixing 20 parts by weight of a compound of general formula(I), 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207),3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 partsby weight of paraffinic mineral oil (boiling range for example approx.255 to above 277° C.), and grinding the mixture in a ball mill to afineness of below 5 microns.

4. Emulsifiable Concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of acompound of general formula (I), 75 parts by weight of cyclohexanone assolvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.

5. Water-Dispersible Granules

Water-dispersible granules are obtained by mixing

75 parts by weight of a compound of general formula (I),

10″ calcium lignosulfonate,

5″ sodium lauryl sulfate,

3″ polyvinyl alcohol and

7″ kaolin,

grinding the mixture in a pinned-disk mill and granulating the powder ina fluidized bed by spraying on water as granulation liquid.

Water-dispersible granules are also obtained by homogenizing andprecomminuting, in a colloid mill,

25 parts by weight of a compound of general formula (I),

5″ sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,

2″ sodium oleoylmethyltauride,

1″ polyvinyl alcohol,

17″ calcium carbonate and

50″ water,

subsequently grinding the mixture in a bead mill, and atomizing anddrying the resulting suspension in a spray tower by means of asingle-substance nozzle.

C. BIOLOGICAL EXAMPLES

1. Pre-Emergence Herbicidal Action Against Harmful Plants

Seeds or rhizome pieces of mono- and dicotyledonous harmful plants areplaced in sandy loam in pots of a diameter of 9 to 13 cm and coveredwith soil. The herbicides, formulated as emulsifiable concentrates ordusts, are applied to the surface of the covering soil in the form ofaqueous dispersions or suspensions or emulsions at an application rateof 300 to 800 l of water/ha (converted), at various dosages. For furthercultivation of the plants, the pots are then kept in a greenhouse underoptimum conditions. The visual scoring of the damage to the harmfulplants is carried out 3-4 weeks after the treatment. As shown by theresults of these comparative tables, the selected compounds according tothe invention have better herbicidal activity against a broad spectrumof economically important mono- and dicotyledonous harmful plants thanthe compounds disclosed in the prior art.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of mono- and dicotyledonous harmful plants are placed in sandyloam in cardboard pots, covered with soil and grown in the greenhouseunder good growth conditions. Two to three weeks after sowing, the testplants are treated at the three-leaf stage. The compounds according tothe invention, which are formulated as wettable powders or as emulsionconcentrates, are sprayed at an application rate of 600 to 800 l ofwater/ha (converted) in a dosage stated in tables 1 to 5 onto thesurface of the green plant parts. After the test plants have been leftto stand in the greenhouse for 3 to 4 weeks under optimum growthconditions, the action of the compounds according to the invention isscored in comparison to compounds disclosed in the prior art. As shownby the results of these comparison tables, the selected compoundsaccording to the invention have better herbicidal activity against abroad spectrum of economically important mono- and dicotyledonousharmful plants than the compounds disclosed in the prior art.

Meanings of the abbreviations used in the comparison tables below:

ABUTH Abutilon theophrasti AMARE Amaranthus retroflexus AVEFA Avenafatua CYPES Cyperus serotinus DIGSA Digitaria sanguinalis ECHCGEchinochloa crus galli GALAP Galium aparine LOLMU Lolium multiflorumMATIN Matricaria inodora PHBPU Pharbitis purpureum POLCO Polygonumconvolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronicapersica VIOTR Viola tricolor XANST Xanthium strumarium

COMPARATIVE TABLE 1 Post-emergence Dosage Activity against harmfulplants Compound No. [g a.i./ha] AMARE POLCO VIOTR XANST

20 90% 90% 100% 80% compound according to the invention

20 70% 40%  70% 50% compound known from WO 98/42678

COMPARATIVE TABLE 2 Post-emergence Dosage Activity against harmfulplants Compound No. [g a.i./ha] SETVI AMARE PHBPU VIOTR

80 100% 100% 70% 90% compound according to the invention

80  0% 70% 40% 70% compound known from WO 98/42678

COMPARATIVE TABLE 3 Post-emergence Dosage Activity against harmfulplants Compound No. [g a.i./ha] SETVI AMARE PHBPU VERPE

20 90% 90% 80% 100% compound according to the invention

20 50% 60% 30%  60% compound known from WO 98/42678

COMPARATIVE TABLE 4 Post-emergence Dosage Activity against harmfulplants Compound No. [g a.i./ha] DIGSA SETVI GALAP VERPE

20 90% 80% 80% 70% compound according to the invention

20 70% 50% 30% 30% compound known from WO 98/42678

COMPARATIVE TABLE 5 Pre-emergence Dosage Activity against harmful plantsCompound No. [g a.i./ha] AVEFA ECHCG SETVI AMARE

80 50% 100% 100% 100% compound according to the invention

80  0%  40%  80%  80% compound known from WO 98/42678

COMPARATIVE TABLE 6 Pre-emergence Activity against Dosage harmful plantsCompound No. [g a.i./ha] ECHCG SETVI

20 90% 60% compound according to the invention

20 60%  0% compound known from WO 98/42678

COMPARATIVE TABLE 7 Pre-emergence Dosage Activity against harmful plantsCompound No. [g a.i./ha] CYPES POLCO VERPE

320 100% 60% 100% compound according to the invention

320  40%  0%  80% compound known from WO 98/42678

COMPARATIVE TABLE 8 Post-emergence Dosage Activity against harmfulplants Compound No. [g a.i./ha] SETVI ABUTH STEME VERPE

20 90% 90% 100% 80% compound according to the invention

20 30% 70%  80% 60% compound known from WO 98/42678

1. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof

in which R¹ is hydrogen, (C₁-C₆)-alkyl or (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl,R² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, di-(C₁-C₄)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl; Y is hydrogen, (C₁-C₆)-alkylsulfonyl,(C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,thiophenyl-2-sulfonyl, benzoyl, (C₁-C₄)-alkylbenzoyl-(C₁-C₆)-alkyl orbenzyl, each of which is substituted by m identical or differentradicals from the group consisting of halogen, (C₁-C₄)-alkyl and(C₁-C₄)-alkoxy, m is 0, 1, 2 or
 3. 2. The4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 1 in which R¹ is hydrogen or (C₁-C₄)-alkyl,R² is (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,di-(C₁-C₂)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl; Y is hydrogen, (C₁-C₃)-alkylsulfonyl,(C₁-C₂)-alkoxy-(C₁-C₄)-alkylsulfonyl, or is phenylsulfonyl,thiophenyl-2-sulfonyl, benzoyl, (C₁-C₄)-alkylbenzoyl-(C₁-C₆)-alkyl orbenzyl, each of which is substituted by m methyl groups, m is 0 or
 1. 3.The 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 1 in which R¹ is hydrogen or (C₁-C₄)-alkyl,R² is (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,di-(C₁-C₂)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl; Y is hydrogen.
 4. A herbicidalcomposition which comprises a herbicidally effective amount of at leastone compound of the formula (I), or a salt thereof, as claimed inclaim
 1. 5. The herbicidal composition as claimed in claim 4 as amixture with formulation auxiliaries.
 6. A method for controllingunwanted plants which comprises applying an effective amount of at leastone compound of the formula (I), or a salt thereof, as claimed in claim1 to a plant or a site of unwanted plant growth.
 7. A method forcontrolling unwanted plants comprising applying an effective amount of aherbicidal composition as claimed in claim 4 to a plant or to a site ofunwanted plant growth.
 8. A method as claimed in claim 7 wherein thecompounds of the formula (I), or a salt thereof, are used forcontrolling unwanted plants in crops of useful plants.
 9. A method asclaimed in claim 8 wherein the useful plants are transgenic usefulplants.
 10. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I) asclaimed in claim 1 wherein, when Y is hydrogen, said4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 1 may occur in one of the followingtautomeric structures:


11. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I) or a saltthereof, as claimed in claim 1 comprising an acidic proton which may beremoved by reaction with a base.
 12. A4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 11 wherein an acidic proton is removed by abase selected from the group consisting of hydrides, hydroxides andcarbonates of lithium, sodium, potassium, magnesium and calcium, andalso ammonia and organic amines.
 13. A4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 1 which is present in the form of a salt.14. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 13 wherein said salt is formed by formingan adduct with an organic acids and/or an inorganic acids.
 15. A4-(3-aminobenzoyl)-1-methylpyrazole of the formula (I), or a saltthereof, as claimed in claim 1 which exists as stereoisomer and/ormixtures thereof.
 16. A 4-(3-aminobenzoyl)-1-methylpyrazole of theformula (I), or a salt thereof, as claimed in claim 1, wherein Ycomprises hydrogen.
 17. A 4-(3-aminobenzoyl)-1-methylpyrazole of theformula (I), or a salt thereof, as claimed in claim 1, wherein R¹comprises hydrogen or methyl.
 18. A 4-(3-aminobenzoyl)-1-methylpyrazoleof the formula (I), or a salt thereof, as claimed in claim 1, wherein R¹comprises hydrogen, methyl, ethyl, propyl, cyclopropyl, or—(CH₂)₃—O—CH₃.
 19. A 4-(3-aminobenzoyl)-1-methylpyrazole of the formula(I), or a salt thereof, as claimed in claim 1, wherein R¹ and R²comprise methyl.
 20. A 4-(3-aminobenzoyl)-1-methylpyrazole of theformula (I), or a salt thereof, as claimed in claim 1, wherein Y ishydrogen; R¹ and R² are methyl.